Gary Vaynerchuk's 2023 takes on investing and building businesses

Executive overview

Most startup advice on founders is oversimplified. The right profile depends on the challenge: consumer brands need business operators; deep tech needs technical founders.

No single founder type wins — context determines who to back.

First-time vs. experienced founders

• Excitement about the market shifts which type Gary prefers
• First-time founders built the best companies he loves
• When less optimistic, he wants proven execution over vision
• Zuckerberg is rare — he had both attributes

Technical vs. business founders

• Direct-to-consumer vs. Procter & Gamble: business founder wins
• Deep AI or Web3 challenges: technical founder wins
• First time in a decade he'd back a technical founder at the frontier

The "number 11 from Netflix" trap

• Avoid backing someone who was #5, 7, or 13 at a big-name company
• Success there doesn't transfer — they're BJ Armstrong, not Michael Jordan
• Only back the #1 or #2 operator from those orgs

Investing in family businesses

• High emotional intelligence and strong gut: back family businesses — 50–70% hit rate
• Without that capability: stay away entirely
• The read depends on the investor's self-awareness, not a universal rule

Co-CEOs vs. single CEOs

• Co-CEOs: the single worst structure in business, full stop
• Multiple co-founders are fine — the question is who's the 1A
• Giving co-founder titles for retention is a legit strategy; co-CEO authority is not

Dirt vs. money: founder background

• Old take: hunger from poverty beats comfort every time
• Updated take: 25% of the time, "comes from money" works — chip on shoulder can be a real driver
• The danger with "comes from nothing": deep insecurity can collapse in the final stretch
• Self-esteem matters more than background; insecurity as a fuel source isn't sustainable

AI vs. Metaverse

• Most AI startups 3–5 years ago were fake AI or just API wrappers — that era is over
• ChatGPT, Jasper, and Google's music AI signal the real wave has arrived
• Metaverse: strategically important but timing is unknowable — 3 years or 22 years out
• Gary's rule: execute on today, keep a side eye on tomorrow

Content creativity

• The mission: find the next creative framework that everyone copies
• Try unused color palettes, new angles, deliberate oddities (e.g., posting content upside down)
• Reference point: the Instagram egg — disruptive simplicity that broke the internet